Ammonia → 4-Methoxycyclohex-3-en-1-ol

HRID 1826213Notes

Reaction equation

HRID 1826213 reaction equation
CC1(C)CO[C:5]2([CH2:11][CH2:10][C:8](=[O:9])[CH2:7][CH2:6]2)[O:4][CH2:3]1.COC1C=CC(O)=CC=1.[Li].N>C(O)C>[CH3:3][O:4][C:5]1[CH2:11][CH2:10][CH:8]([OH:9])[CH2:7][CH:6]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 90154-MethoxyphenolHCID 5879683,3-Dimethyl-1,5-dioxaspiro(5.5)undecan-9-oneHCID 3028194Lithium

Product 1

HCID 124521944-Methoxycyclohex-3-en-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Journal of Synthetic Communications 9(2), 123–127 (1979) disclosed a process for the preparation of 1,4-cyclohexane dione mono-2,2-dimethyl trimethylene ketal using Birch reduction of 4-methoxy phenol with lithium and ammonia in presence of ethanol to yield 4-methoxy-3-cyclohexene-1-ol, which is further reacted with neopentyl glycol using PTSA in benzene medium gave 2,3-dimethyl-1,3-dipropylene ketal of 4-hydroxycyclohexanone. Oxidation of the resulting ketal with pyridinium chlorochromate yields the 1,4-cyclohexanedione mono-2,2-dimethyl trimethylene ketal. Journal of Synthetic Communications, 14 (1), 39–44 (1984) disclosed a process for preparation of 1,4-cyclohexanedione mono-2,2-dimethyl trimethylene ketal that includes continuous extraction of an aqueous solution of 1,4-cyclohexane dione containing 2,2-dimethyl-1,3-propane diol in molar excess and sulfuric acid as the catalyst to afford the 1,4 cyclohexanedione mono-2,2-dimethyl trimethylene ketal. Nevertheless, there is still a need for an improved process suitable for a commercial scale production of 1,4-cyclohexanedione mono-2,2-dimethyl trimethylene ketal

Sources & evidence

ORD record
ord-cb77cab5d932495caf6504d19397d8e3
Source dataset
uspto-grants-2006_05
Patent number
US07049448B2

Reaction notes

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