Water → HCID 12475277, compound

HRID 1941230Notes

Reaction equation

CC(C)([O-])C.[K+].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:16])[CH3:15].[C:17](=S)=[S:18].O>C1C=CC=CC=1>[SH:18][C:17]1[O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14](=[O:16])[CH:15]=1

Participants

Conditions

Temperature: 15 °C

Procedure

Part A: Potassium t-butoxide (134 g, 1.2 mole) is covered with benzene (1 L) in a flame dried round bottom flask equipped with an overhead stirrer, addition funnel, thermometer, and a nitrogen inlet. This suspension is maintained at 15° C. A solution of o-hydroxyacetophenone (54.4 g, 48.1 ml, 0.4 mole) and carbon disulfide (30.4, 24 ml, 0.4 mole) in benzene (700 ml) is slowly added over 1.3 hours, applying an ice bath periodically in order to maintain the temperature 18° C. The slurry which forms is stirred at ambient temperature for one day. The reaction mixture is transferred to a separatory funnel containing water (4 L) and extracted with ether (4×250 ml) and EtOAc (3×250 ml). The aqueous layer is acidified with 10% H2SO4 (1 L) and stirred at ambient temperature overnight. The resulting solid is filtered off and dried in vacuo at 50° C. overnight to yield 22.07 g of 2-mercapto-4H-1-benzopyran-4-one. Mp 207°-8° C.

Workup

customdried round bottom flask
customequipped with an overhead stirrer, addition funnel
temperatureto maintain the temperature 18° C
customThe reaction mixture is transferred to a separatory funnel
extractionextracted with ether (4×250 ml) and EtOAc (3×250 ml)
stirringstirred at ambient temperature overnight
filtrationThe resulting solid is filtered off
customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record: ord-778b2beb56b949129ae6133c55e4cc66
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05703075

Reaction notes

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