Potassium Hydroxide → 6-Benzyloxy-2,2-dimethyl-3,4-epoxychroman

HRID 613437Notes

Reaction equation

HRID 613437 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH:13](Br)[CH:12]2[OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH:13]1[O:22][CH:12]21)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 195933326-Benzyloxy-3-bromo-2,2-dimethyl-chroman-4-ol

Product 1

HCID 109240076-Benzyloxy-2,2-dimethyl-3,4-epoxychromanYield 103.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9.5 g (28.5 mmol) of 6-benzyloxy-3-bromo-2,2-dimethyl-chroman-4-ol in 100 ml of THF was stirred overnight with 4.6 g (82 mmol) of potassium hydroxide powder. The batch was subsequently filtered through Celite and the filtrate was concentrated using a rotary evaporator, giving 8.3 g of 6-benzyloxy-2,2-dimethyl-3,4-epoxychroman, m.p. 70-72° C.

Workup

  1. filtrationThe batch was subsequently filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customa rotary evaporator

Sources & evidence

ORD record
ord-abff71dbd7f342b5984830f7423c0340
Source dataset
uspto-grants-1999_12
Patent number
US06008245

Reaction notes

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