Benzyl Alcohol → Benzyl 6-hydroxyhexanoate

HRID 1289869Notes

Reaction equation

HRID 1289869 reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1([CH2:15][OH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>S(=O)(=O)(O)O>[C:9]1([CH2:15][O:16][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 10401epsilon-CAPROLACTONE

Product 1

HCID 15224618Benzyl 6-hydroxyhexanoateYield 26%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
50 °C

Procedure

A mixture of 6-hexanolactone (40 g, 0.35 mol), phenylmethanol (70 g, 0.647 mol), and conc. sulfuric acid (40 drops) was heated at 50° C. overnight. The resulting mixture was purified by column chromatography (hexane, 5-30% ethyl acetate/hexane) and distilled to afford 20.1 g (26%) of 6-hydroxyhexanoic acid phenylmethyl ester, b.p. 70°-75° C./1 mm.

Workup

  1. customThe resulting mixture was purified by column chromatography (hexane, 5-30% ethyl acetate/hexane)
  2. distillationdistilled

Sources & evidence

ORD record
ord-88b4421ed80245eca151443e737e1075
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

Loading…